Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR5170)
Drug Name
Levorphanol
Synonyms
levorphanol; Levorphan; Methorphinan; Aromarone; Racemethorphanum; Dromoran; Cetarin; Antalgin; Levo-Dromoran; Racemic dromoran; Methorfinan [Czech]; Levorfanolo [DCIT]; Levorphanolum; Levorfanol; Orphan; Levorfanol [INN-Spanish]; Levorphanolum [INN-Latin]; Racemorfano [INN-Spanish]; 17-Methylmorphinan-3-ol; N-Methyl-3-hydroxymorphinan; Racemorphan; Racemorphan [INN:BAN]; Racemorphane [INN-French]; Racemorphanum [INN-Latin]; (-)-N-Methylmorphinan-3-ol; Morphinan-3-ol, 17-methyl-; Levorphanal; dl-3-Hydroxy-N-methylmorphinan; DEA No; Antalgin; DEXTRORPHAN; Levodroman; Levorfanolo; Methorfinan; Racemorfano; Racemorphane; Racemorphanum; NU 2206; L-Dromoran; Levorphanol (INN); Ro 1-5431; Levo-Dromoran (TN); Dl-3-Hydroxy-N-methylmorphinan; (+)-3-Hydroxy-17-methylmorphinan; (+-)-17-Methylmorphinan-3-ol; (+-)-3-Hydroxy-N-methylmorphinan; (-)-3-Hydroxy-N-methylmorphinan; 1,3,4,9,10,10a-Hexahydro-11-methyl-2H-10,4a-iminoethanophenanthren-6-ol, dl-mixture; 1,3,4,9,10,10a-Hexahydro-6-hydroxy-2H-10,4a-(iminoethano)-11-methylphenanthrene; 3-Hydroxy-N-methylmorphinan; Dextrorphan
Indication Pain [ICD11: MG30-MG3Z] Approved [1]
Cerebral stroke [ICD11: ICD11: 8B11] Terminated [2]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 257.37 Topological Polar Surface Area 23.5
Heavy Atom Count 19 Rotatable Bond Count 0
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
5359272
ChEBI ID
CHEBI:6444
CAS Number
297-90-5
TTD Drug ID
D0T3HY
Formula
C17H23NO
Canonical SMILES
CN1CC[C@]23CCCC[C@H]2[C@H]1CC4=C3C=C(C=C4)O
InChI
InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m0/s1
InChIKey
JAQUASYNZVUNQP-USXIJHARSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
3-hydroxymorphinan DM000826
5463854
Unclear - Unclear 1 [3]
Levorphanol Metabolite M3 DM018539 N. A. Unclear - Unclear 1 [3]
Levorphanol Metabolite M4 DM018536 N. A. Unclear - Unclear 1 [3]
Levorphanol Metabolite M5 DM018538 N. A. Unclear - Unclear 1 [3]
Levorphanol Metabolite M7 DM018535 N. A. Unclear - Unclear 2 [3]
Levorphanol Metabolite M8 DM018537 N. A. Unclear - Unclear 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR010613 Levorphanol Levorphanol Metabolite M6 Unclear - Unclear Unclear [3]
MR010615 Levorphanol Levorphanol Metabolite M4 Unclear - Unclear Unclear [3]
MR010617 Levorphanol Levorphanol Metabolite M5 Unclear - Unclear Unclear [3]
MR010618 Levorphanol Levorphanol Metabolite M3 Unclear - Unclear Unclear [3]
MR010616 Levorphanol Metabolite M4 Levorphanol Metabolite M8 Unclear - Unclear Unclear [3]
MR010614 Levorphanol Metabolite M6 Levorphanol Metabolite M7 Unclear - Unclear Unclear [3]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
UDP-glucuronyltransferase (UGT) DMEN064 . Not Available Not Available [4]
References
1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800009336)
3 Exploration of catalytic properties of CYP2D6 and CYP3A4 through metabolic studies of levorphanol and levallorphan
4 Metabolism and disposition of prescription opioids: a review. Forensic Sci Rev. 2015 Jul;27(2):115-45.

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